• Leslie

Beautiful Must See Bucket List Towns in Italy

Updated: Sep 18

"Life is a combination of magic and pasta." -- Frederico Fellini


pretty pastel houses in Cinque Terre


Bella Italia! Italy is one of my favorite countries, a dream destination I could return to time and time again. Italy has Europe's richest and most ancient culture. After all, Italy is the cradle of European civilization — founded by the Roman Empire and embellished by the Roman Catholic Church.


As you explore Italy, you'll confront some of the world's most iconic monuments -- Roman ruins, UNESCO sites, Renaissance masterpieces, elegant medieval towns. But you'll also find jaw dropping landscapes and magical seaside hamlets.


In this guide, I take you on a curated tour of 25 of Italy's most beautiful and charming towns. I've left out Rome because, as such big city, it deserves special treatment. I've spilled so much ink over the eternally fascinating Eternal City, it's hard to fathom. So, now, I delight you with Italy's smaller charming gems.



the famous Ponte Vecchio over the Arno River in Florence


25 Most Beautiful Towns In Italy For Your Bucket List


1. Florence: Renaissance Marvel


I'll start with my favorite town in Italy, Florence. Florence is an overwhelmingly beautiful city, the "Cradle of the Renaissance." With the best Medieval and Renaissance art in Europe, Florence is a veritable art lovers paradise.


Florence is a city that's alive, sensual, and romantic. You can be seduced by Botticelli and awed by Michelangelo, in a time tunnel experience. Not surprisingly, Florence's entire city center is a designated UNESCO site. There are scads of must see sites in Florence.


You can visit frescoed churches, majestic cathedrals, elegant palaces and piazzas, and world class museums. And tread on the same flagstones as Leonardo, Dante, and Galileo.



the iconic Brunelleschi dome of Florence cathedral

Michelangelo's David in the Galleria dell'Accademia


Florence Cathedral is the most prominent landmark in Florence. It was built over 172 years, beginning in 1296. Florence Cathedral is Gothic in style, but not in the light and elegant way you think of Paris' Notre Dame. It's made of brown sandstone and beautifully frosted with pink, green, and white marble.


If you buy a combination ticket for the entire Duomo complex, you can also visit and/or climb Brunelleschi's dome, Giotto's Bell Tower, the dazzling Baptistry, and the Duomo museum.


Spend some time lingering in the Piazza della Signoria, Florence's free outdoor sculpture gallery. Head inside the Palazzo Vecchio, former home of the Medici dynasty, and admire the frescos by Giorgio Vasari.


You can't leave Florence without visiting the Uffizi Gallery. It's a bastion of Renaissance art with one of the world's most famous paintings, Botticelli's Birth of Venus.


If you're a real art fan, plan to see Michelangelo's iconic David in the Galleria dell'Accademia and the sculptures of the Bargello Museum. Or, if you like to travel with a theme, you can follow the Michelangelo trail in Florence.



6th century mosaics in the main apse of the Basilica of Sant Apolinare in Classe


2. Ravenna: Magical Mosaics

Ravenna was once the epicenter of the Western World, when the Byzantine Empire made Ravenna its capitol. The Byzantine rulers blanketed Ravenna's churches with gorgeous mosaics. Ravenna boasts the best early Christian mosaics in the world. This artistic legacy rivals Venice or Istanbul, making Ravenna a UNESCO site in 1996.


If, like me, you feel compelled to admire these glittering gems, these are the must see sites in Ravenna: (1) the Basilica of Sant'Apollinare in Classe; (2) the Basilica of Sant'Apollinare Nuovo; (3) the Basilica of San Vitale; (4) the Neonian Baptistery, (5) the Mausoleum of Galla Placidia, and (6) the Archbishop's Chapel.


You can visit these sites with a combination ticket. The best mosaics are in the Basilica of San Vitale, built by the Emperor Justinian in 540. It's a separate national museum with an entry fee of 10.50.


Ravenna's most famous son is Dante Alighieri, the author of the Divine Comedy and father of the Italian language. The poet spent the last three years of his life in Ravenna, after being expelled from Florence when he fell out of political favor. You can visit Dante's tomb, a small neoclassical temple right next to the Basilica of San Francesco.


Click here for my complete guide to Ravenna.



beautiful homes in Mantua


3. Mantua: Renaissance Haven


Italy is usually overflowing with tourists. But in the tiny undiscovered village of Mantua the world is still and quiet. Mantua must surely be one of Europe's best kept secrets.


Mantua lies in the north of Italy in the Lombardy region, surrounded by three lakes. It's a fairly easy day trip from Milan or Verona. Mantua is the perfect place for strolling -- with arcaded streets, cobbled lanes squares, and graceful buildings.


What makes Mantua especially dreamy is its Renaissance architecture, courtesy of the aristocratic Gonzaga family who ruled Mantua for four centuries. Here, you'll find the grand Ducal Palace, the Te Palace, St. Peter Cathedral, the Teatro Bivbiena, and the Rotuno of San Lorenzo. For a tiny place, it's just amazing.


Mantua's most famed site is the Ducal Palace or Palazzo Ducale. It's the second largest residential building in Europe, after the Vatican. It's a massive fortress-like residence. Inside, there'a maze of 600 ornate gilded, frescoed, and marbled rooms, topped with a Hall of Mirrors.



the walled village of Monteriggioni in Tuscany


4. Monteriggioni: Walled Village


Monteriggioni is an idyllic walled town in the Tuscany. Just look how charming it is. It almost doesn't look real. Monteriggioni was built by Sienna in the 13th century as a defense in its ongoing conflict with its arch rival, Florence.


There's an upper and a lower parking lot. It's especially pretty in the early morning or at sunset. 4 euros gets you entry to the walls and the museum onsite. You only need an hour or two. If you want to have lunch or dinner, try Il Pozzo.


If you're a fan of Assassin’s Creed, you'll be glad to know that Monteriggioni is real (though much smaller than depicted there). The town also makes an appearance in Dante's Divine Comedy. Dante compares the spiky turrets of Monteriggioni to giants surrounding the abyss.



the Maritime Theatre in Hadrian's Villa in Tivoli


5. Tivoli: UNESCO Sites


Historic Tivoli lies just 20 miles east of Rome on the edge of the Sabine Hills. Tivoli is the perfect day trip from Rome, especially for archeology lovers and history buffs.


Tivoli is home to two UNESCO World Heritage Sites: the sprawling Hadrian's Villa, and the comely 16th century Villa d'Este, a Renaissance retreat. If you're fond of ancient history or are ruin luster like me, you'll be fascinated and thrilled by the evocative ruins of Hadrian's Villa.



the Fountain of the organ at Villa d'Este

me at the Canopus of Hadrian's Villa


Hadrian's Villa is an important archeological complex. It was the largest and most spectacular palace of ancient Rome, three times the size of Pompeii. It reflected the power and glory of ancient Rome and the world's most important leader, Emperor Hadrian. And it was designed by Hadrian himself, who fancied himself an amateur architect.


If you have ruin fatigue, the next door late Renaissance estate, Villa d'Este, is a delicious escape. Villa d'Este is a playground of whimsy, topped with a frescoed villa and a sweet honeysuckle breeze. The gardens are filled with sparkling fountains, moss draped grottos, and ponds filled with water lilies.



Stresa


6. Stresa: Italian Lake District


The Italian lake district is one of Italy's prettiest regions, situated in the shadow of the Alps. The main lakes are Lake Como, Lake Garda and Lake Maggiore. Most people settle in at the swishiest village, magical Bellagio on Lake Como. But on the western Lake Maggiore you'll find a real treasure -- Stresa.


Elegant laid back Stresa is easy to fall in love with. Grandiose villas line the waterfront promenade, which is made for leisurely strolling. The medieval streets are a delightful tangle.


But the best thing to do in Stresa is ferry over to the tiny off shore Borromean Islands -- Isola Bella, Isola dei Pescatori, and Isolar Madre. They're open to the public between mid March and mid October. The highlight is the Borromeo Palace on Isola Bella with an 80 foot dome.


The powerful Borromeo family, like the Gazagos, were Lombardian aristocrats. Lake Maggiore was their personal playground. Their grand palace on Isola Bella is a Renaissance masterpiece. Inside it's exquisite, with an 8th century grotto, decorated floor to ceiling with shell motifs and mosaics. The terraced Italianate gardens are just luscious, with a wafting scent of jasmine floating in the air.



Civita di Bagnoregio


7. Civita di Bagnoregio: Tiny Hilltop Village


The Etruscans founded Civita di Bagnoregio over 2500 years ago and it's largely unaltered ever since. The isolated and picturesque Civita teeters on a hilltop in a vast canyon, north of Rome. The topography scares away most tourists.


To access this little hamlet, you'll have to ditch your car, walk across an elevated and steep 300 meter pedestrian bridge, and enter via a massive 12th century stone arch called the Porta Santa Maria. What could be more dreamy and surreal?


Once inside, the charms of Civita are subtle. There's nothing special to do but look around in this rural village. It's just unadulterated old world Italy. The warm stone walls glow in the sunshine. Have a seat on the steps of San Donato Church, be suspended in time, and admire the flowerpots.



panoramic view of the historic upper city of Bergamo


8. Bergamo: for Architecture Lovers


Bergamo is a small town in Italy's Lombardy region, located between Milan and Lake Como. Bergamo outshines Italy's capital in beauty and graceful architecture. The town makes a great base for touring northern Italy. But aside from its geographic convenience, Bergamo is a fascinating historical city.


Bergamo has an upper and lower city. Naturally, the upper city, or Citta Alta, is the older Renaissancey part of town. Start off with a walk around the 16th century Venetian Walls. The vibrant center of Bergamo is Piazza Vecchia. There, you'll find every manner of shop, cafe, and restaurant.


The other must see square is the Piazza del Duomo. Walk throughs he archways of the Palazzo della Ragione and you'll reach it. The square boasts the beautiful Basilica of Santa Maria Maggiore. Go inside! You enter through a portico with Venetian lions into an extravaganza of Baroque gilding and Renaissance tapestries.


To the right of the basilica lies the even more impressive Colleoni Chapel. Sporting a pink and white marble facade, the chapel stands out with a combination of Renaissance, Mannerist, and Baroque architectural elements.



view of the medieval walls and towers of Orvieto


9. Orvieto: Celebrated Cathedral town


Charming Orvieto is the capitol of Umbria. It's set high above a volcanic outcropping and chock full of medieval buildings. Nothing much has changed in this rustic fairytale town in 500 years.


The main drag in Orvieto is the Corso Cavour. In the town center, the Torre del Moro, a 13th century civic landmark, towers above. An elevator and another 171 steps get you to the top where you'll have panoramic views.



the beautiful facade of Orvieto Cathedral


Orvieto's piece de resistance is its magnificent cathedral. Orvieto Cathedral is one of the most beautiful and ancient churches in Italy. It's a riveting ensemble of spires, spikes, golden mosaics, statuary, stained glass, and black and white striped marble. And that's just the facade.


Inside, the Chapel of San Brizio has one of the Renaissance's greatest fresco cycles by Luca Signorelli. Michelangelo came to inspect the chapel before beginning his own master work, the Sistine Chapel in the Vatican Museums. The frescos depict the usual religious themes -- temptation, damnation, and salvation.



view of Siena's Duomo complex


10. Siena: a Burnt Orange UNESCO Wonder


Siena is one of the best cities to visit in Tuscany for its rustic medieval beauty, tasty food, and luscious chianti. If you want to bask in medieval times, there's no better place. Spend at least one day in Siena. I guarantee you'll fall in love.


You'll want to spend ample time strolling through the pedestrianized historic center. It's a well-preserved burnt orange dream littered with cute cafes and shops.


Siena's most famous site is its Duomo, Siena Cathedral. It's one of Europe's most beautiful churches, especially for lovers of all things Gothic. It's the symbol of Siena, clad all over in Siena's trademark white and dark green marble. Consistent with the Gothic ethos that "more is always better," every inch is decorated with marble, mosaics, sculptures, and frescos.



restaurants lining the Piazza del Campo

the Palazzo Pubblico in Piazza del Campo


To visit the Siena Duomo complex properly, you need to pre-purchase the Opa Si Pass. The Duomo complex isn't just Siena Cathedral. It also includes the Baptistry, the Crypt, the Piccolomini Library, the Facciatone viewing terrace, and the Museo dell'Opera del Duomo Museum. The Facciatone offers stunning views.


Don't forget to tour Siena's town hall, the Palazzo Pubblico. It was built in 1297-1308 for the Council of Nine, the governing body of Siena. The palazzo is one of the seminal civic structures in Europe It's a harmonious example of early Renaissance architecture, with a curved brick facade and beautiful triforate arched windows.


Inside, you'll find the Allegory of Good and Bad Government, one of the most famous frescos in Italy. Beside the palazzo soars the slender Tower of Mangia, which you can climb for panoramic views.


Click here for my guide to spending an efficient 24 hours in Siena.



the dramatic coastline of Capri


11. Capri: Roman Ruins & Grottos


Rugged mountainous Capri is one of the world's most glamorous islands. It was made famous as the vacation hideaway of the Roman emperors. Capri was also a popular stop for the wealthy on their "grand tour of Europe." Today, it's crowded. But even with the crowds, it's drop dead gorgeous, set on a glittering blue sea.


The center of life in Capri is the Piazzettta. Often overflowing with crowds, it's been called "the world's living room."


If you love Roman ruins more than exclusive boutiques, head to Villa Jova, a fantastic archaeological site. Emperor Tiberius was the reluctant heir of Rome's first emperor, Augustus. But he was a military man, not suited for Rome's internecine politics. Eventually, he abandoned Rome for his swishy villa perched precipitously on Capri's rosemary scented cliffs.


Most people indulge in a Blue Grotto boat tour, though it can be a tourist trap extraordinaire. If the sea waters are calm, you transfer from your motor boat into a row boat and enter the cave. Then, the magical colors of the water and walls envelope you.



ruins of a Roman amphitheater in Lecce


12. Lecce: the Florence of the South


Located in the radiant Puglia region of Italy, beautiful Lecce is known as the Florence of the South. The historic center is constructed from Lecce stone, a local golden limestone, and decorated with ebullient Baroque architecture. The city's history dates back to Roman times, though it was largely constructed in the mid 17th century.


Lecce is easy to explore on foot. Begin in the monumental Piazza Sant'Orozio where a 2nd century Roman column looms above. At the southern end of the piazza, there's the ruins of an ancient Roman amphitheater, dating from either the 1st or 2nd century. It originally seated 25,000 screaming patrons enjoying the gory games between gladiators and beasties.


Lecce also a string of ornate Baroque churches, along Via Vittorio Emanuele and Via Giuseppe Libertini. The most famous church in town is the Basilica of Santa Croce. While it's not as renowned as the Basilica of Santa Croce in Florence, it's of a different vintage, overflowing with Baroque ornamentation. Lecce also has a Duomo, with a 12th century chiseled facade.



aerial view of Sorrento coastline


13. Sorrento: Lemon Lively


Wedged on a ledge over the sea, the cliff top town of Sorrento makes a perfect springboard for visiting the Amalfi Coast. You can day trip to Pompeii, Positano, Capri, and even Naples.


Start your tour of Sorrento on Piazza Torquato Tasso. Named after an Italian poet, this is the center of life in Sorrento. Tasso's statue sits in the Piazza Sant'Antonio. But the hidden back lanes of Sorrento are the most tantalizing, filled with shops selling gelato, limoncello, prosecco, leather goods, and more.


If you're ready to sit down and sip, the Hotel Belair Sorrento offers stunning views overlooking Sorrento and Mount Vesuvius. There's also good views from La Pergola Bar a Champagne.


If you need some beach time, head to Marina Grande Beach. Sorrento is also famous for its lemons and filled with lemon groves.



the seaside town of Santa Margherita


14. Santa Margherita: Portofino Alternative


The Italian Riviera is known for its colorful seaside towns. While most people flock to Cinque Terre, Santa Margherita is just as beautiful and less crowded. And much less glitzy than its elegant neighbor Portofino.


Santa Margherita has a pretty palm lined waterfront. Cafes line the town's two seaside squares, Piazza Martini della Liberta and Piazza Vittorio Veneto. The only landmark of note is the Basilica of Sant Margherita, worth a look for its gilded and chandelier interior.


If you want a picturesque hike or run, a well traveled trail connects Santa Margherita with Portofino. It can be done as a one way hike with a return via water taxi or bus, or as a return trip on foot as well. Along the way, you can snap photos of the splendid countryside.



pastel houses cascading down the hills in Positano


15. Positano: Amalfi Coast Superstar

There's a saying that Positano "bites deep," it's so dreamy. This picturesque Amalfi Coast town comes complete with sherbet colored cliffside homes, stunning beaches, and tiny cobbled lanes.


Positano is built for walking. Positano's most famous site is the Church of Santa Maria Assunta, which has a dome made of sparkling majolica tiles.


One of the best things to do in Positano is to hike the Path of Gods. It's a well marked path extending from Positano to the town of Amalfi, which takes about 2 hours. You'll be rewarded with breathtaking views from the trail.



panoramic view of the Ponte Pietra on the Adige River in Verona


16. Verona: Roman & Ruins


This pretty Italian town is full of red and peach colored medieval buildings and Roman ruins. It was made famous by Shakespeare's plays Romeo and Juliet and The Two Men of Verona. And it's a fitting site for a high octane infusion of romance.


Juliet's House, or Casa de Giulietta, is a gorgeous 14th Gothic building in Verona. But, like the fictional love story, Juliet's House is itself a fiction. It wasn't owned by the Capulets.



my daughter and a friend enjoying Juliet's balcony


Piazza dei Signori, with a statue of the poet Dante


Juliet's House is really a manufactured site, scorned by hard core skeptics. But the character of Juliet, nonetheless, has a grip on most of our collective psyche. It's a rarified symbol of love in an often cynical world. Juliet's Wall is covered with notes, scribbles, and love letters.


Once you've made the obligatory Juliet pilgrimmage, you'll also want to tour the doughty Roman Arena, the Arena di Verona, in the Piazza Bra. It's the third largest classical arena in Italy, after Rome's Colosseum and Capua's Colosseum.


You should also stroll through Verona's picturesque piazzas, the Piazza dei Signori (with a statue of Dante) and the Piazza dell Erbe (with a statue of another poet, Barbarani). Visit the Church San Zeno Maggiore, where Romeo and Juliet were fictionally married. And cross the absolutely stunning Ponte Pietra stone bridge.



the towers of San Gimignano


17. San Gimignano: Spiky Towers & Black Death Frescos


Surrounded by cypress groves, San Gimignano is the perfect stop between Siena and Florence. Nicknamed the "Medieval Manhattan," the walled town has a startling cityscape with 13 spiky towers poking the sky. The most famous tower is the Torre Grossa. Climbing to the top is a must do.


San Gimignano dates back to the ancient Etruscans, a civilization that preceded ancient Rome. The town flourished in the middle ages, amassing wealth from saffron.


Sam Gimignano's historic center is a UNESCO site. Park outside the city walls and walk into the town. The central square is the Piazza del Duomo.



the Piazza del Duomo

frescos in the Duomo


In the piazza, you'll find the Collegiate Church of Santa Mary of the Assumption. Consecrated in 1148, it's a beautiful (mostly) Romanesque church, austere on the outside with a feast of frescos on the inside.


In the Chapel of Saint Fina, there are paintings by early Renaissance master Ghirlandaio. There's also a violent fresco cycle of Black Death paintings, possibly by the mysterious artist Barna Da Siena, who allegedly fell to his death from scaffolding while painting the frescos.


After taking in the frescos, stop for a glass of wine or gelato in the Piazza della Cisterna. Be forewarned, Gelateria Dondoli is a very popular spot.



cityscape of Lucca


18. Lucca: Subtle Charmer


Beautifuly preserved Lucca is still entirely contained within its stout Renaissance walls. Happily, Lucca never tore them down, like many Italian towns did to make way for modernity. Now, the walls are like a circular park for pedestrians and bikers. Walking the entire wall takes about 1 hour.


Lucca doesn't really have any must see sites, which means its under the radar for most tourists. Lucca's appeal lies in its relaxed old world charm. It's best to stroll along the pretty streets and piazzas. Romanesque churches are around every corner.


The main pedestrian drag is Via Fillungo. Lucca's central square, Piazza Anfiteatro, was build around an ancient Roman arena. There's no remnants of the arena. But the handsome oval curve -- ringed with yellow medieval buildings -- still sits pretty.



Piazza Anfiteatro


In Piazza San Michele, you'll find the lovely Church of San Michele, with a Romanesque facade. In Piazza San Martino, you'll find the ancient Cathedral of San Martino, which was built to house one of Christendome's most famous relics, the Volto Santo. It was reputedly carved by Nicodemus, the man who helped depose Christ from the cross. The relic is kept in the freestanding Tempietto.


In its heyday, Lucca had over 100 towers, reminding me of Regensburg Germany. They were the homes of wealthy merchants families.The tallest surviving tower, the Torre delle Ore, is fetchingly capped with a bushy forest.



Giotto frescos in Padua's Scrovegni Chapel


19. Padua: Giotto Frescos


Padua is a pretty university town just an hour from Venice. It boasts one of the greatest treasures in Western art, the Scrovegni Chapel, as known as the Arena chapel. Honestly, it's worth a trip to Padua just to see this one site.


Wallpapered with exquisite frescos by Giotto, the Scrovegni Chapel is a precious masterpiece of Italian art. Giotto painted a cycle of 39 frescos depicting the lives of Mary and Jesus in 1303-05. It's as stunning in person as the Sistine Chapel in the Vatican Museums.


Giotto was the greatest painter of the 14th century. His Scrovegni frescos were a watershed moment in art history. With their naturalism, the chapel is considered one of the first examples of "modern art" and profoundly influenced subsequent Renaissance painters.


Visiting the Scrovegni Chapel can be a complicated affair. Click here for my complete guide to the Scrovegni Chapel, with tips for visiting and getting tickets.



aerial view of the historic center of Brescia


20. Brescia: Underrated City destination


Nestled at the foot of the Alps in northern Italy, just a few miles from Lake Como, Brescia is chock full of impressive monuments. Your first point of call is Piazza Paolo VI, formerly called Piazza del Duomo. The square holds not one but two cathedrals.


The Old Cathedral, locally known as Duomo Vecchio, is truly incredible. Building began in the 11th century, with much subsequent construction. The New Cathedral, with Baroque and Neo-Classical designs, was built in the 17th and 18th centuries. It boasts one of Italy's biggest domes.


Piazza della Loggia is another beautiful and elegant square. It's surrounded with Venetian style buildings, including the Renaissance Palazzo della Loggia. Like the Palazzo Pubblico in Siena, it was intended to be an emblem of good government.


Another must see site in Brescia is the Tempio Capitolino, built by Emperor Vespasian in 73 AD. It was dedicated to the Gods Juno, Jupiter and Minerva. Six of the ancient columns still stand.



colorful houses by the water canal at Burano Island near Venice


21. Burano: Italy's Most Colorful Town


Burano makes a beautiful -- and astonishingly colorful -- day trip from Venice, by vaporetto or water taxi. There are no real must see sites in Murano. It's mostly a place to wander around.


Every house in rainbow Burano is painted a different color. You have fabulous views of the pastel weathered homes from the bridges. But don't neglect Burano's side streets.


If you want some things to do in Burano, admire the leaning bell tower, visit the Burano Lace Museum, shop for lace, or visit Bepi's house painted in geometric designs. Burano's culinary speciality is spaghetti al nero with black ink squid. If you'd like a real meal, try Al Gatto Negro.



beautiful architecture in the old town of Bologna


22. Bologna: Pasta & Porticos


Nicknamed La Grassa, or the Big Fat, for its delicious food, Bologna just oozes medieval charm. Bologna is a bit of a hidden gem in Italy. But it shouldn't be. Bologna is a historic city filled with striking architecture, beautiful piazzas, a swathe of palaces and towers, and gourmet restaurants.


Bologna's must see sites are found in the city's main square, Piazza Maggiore. You'll be greeted by a huge statue of Neptune atop a fountain. It was created by one of the great late Renaissance sculptors, Giambologna, who was second only to Michelangelo in skill.


On one end of the piazza is the massive Basilica of San Petronio, honoring Bologna's patron saint. On the other is the swishy Palazzo dei Rei Enzo.



the terra cotta arcaded portico in Bologna

beautiful pastel houses in historic Bologna


Bologna's most famous site and most beautiful church is the Santo Stefano Church. It's a complex of seven churches, founded by Petronio atop a Roman temple. Legend holds that, when Dante was expelled from Florence for his politics, he wiled away time in the Romanesque cloisters.


When you've seen the main sites, head to the Piazza della Mercanzia where Bologna's leaning tower, Asinelli Tower, presides. You can climb 500 steps to the top for panoramic views. Have a gelato or meal in the pretty piazza.


Then head to Bologna's medieval Quadrilatero and meander through the medieval lanes filled with shops. Be sure to walk under the famous 666 Portico, the beautiful terra cotta arcades.



aerial view of Assisi


23. Assisi: A Saintly Stunner With Giotto Frescos


Located in Umbria, the stunning hill town of Assisi is a destination for art lovers. Because Assisi was the home and final resting place of St. Francis, it's also a pilgrimage destination. In fact, the 13th century Basilica of St. Francis of Assisi is one of Italy's best known churches.


This must see Assisi site is two churches in one, both massive and multi-level. You'll want to see the lower church (for pilgrims), the pillar tomb of St. Francis, frescos by many artists, the cloister, and the upper church (for clergy).


The frescos are significant because they mark the transition from the Gothic period of art history to the early Renaissance. Artistically, Assisi could be considered a mini Rome. Like Rome's Basilica of St. Peter, all the most famous artists of the day came to paint the Basilica of St. Francis.


The highlight of the lower church is Giotto's frescos in the Chapel of Santa Maria Maddalena, showing the life of St. Mary Magdalene. That chapel also has a fresco cycle by Pietro Lorenzetti, with a haunting Depostion.


In 1997, after an earthquake prompted restoration of the basilica, some other early Giotto frescos were discovered in the lower church's Chapel of St. Nicholas. They were attributed to Giotto after his initials were found on one paintings. But some critics say the restoration was clumsy and ruined portions of the medieval frescos.


Giotto fresco in the Basilica of San Francisco


When you enter the upper church, you'll encounter paintings by Cimabue, the greatest Italian painter of the 13th century International Gothic style. Giotto, who was Cimabue's protege, also painted a 28 panel cycle called The Life of St. Francis, painted between 1297 and 1300. It's worth noting however that some scholars dispute the attribution.


When you're done exploring the famed basilica, head to the Piazza del Commune. It rivals the Piazza Navona in Rome and the Piazza del Campo in Siena for sheer beauty. If you're hungry, there's an excellent wine and food shop, Botega dei Sapori.


While you're there, step into the Temple of Minerva. Though the Roman temple has now been converted into a church, the facade, including the Corinthian columns, is authentic and over 2000 years old.



the Piazza dell Repubblica in Cortona


24. Cortona: A Crowd Free Tuscan Charmer


If you want to get off the beaten path in Italy, you can go "Under the Tuscan Sun" in hilly Cortona. A former Etruscan town, Cortona was featured in the famous movie and book. It's a quiet charmer, seated on a commanding hill with great views in every direction.


Cortona's main street is Via Nazionale, the only flat place in town. At one end of the streets is Cortona's most famous piazza, the Piazza dell Repubblica. At the other lies the splendid Piazza Garibaldi.


As you walk the small streets, you'll bump into one small church after another. Most of the buildings are made of pietra serena, a type of limestone that famed Italian architect Brunelescchi liked to build with. If you continue on Via Berrettini, you'll reach Fortezza Medicea di Girifalco, which offer splendid views over the countryside.



a street amid the ruins of Pompeii, with a public fountain in the center


25. Pompeii: Relive Daily Life in Ancient Rome


No visit to Italy is complete without a trip to the iconic ruins of Pompeii. Pompeii is Rome's most famous archaeological site, a living museum locked in time.


On August 24, 79, Mount Vesuvius erupted and buried the city in 60 feet of ash. The city was entombed for many centuries. Beginning in 1748, archaeologists began painstakingly excavating the ruins.


The ruins are a remarkable evocation of everyday life. You can get a vicarious thrill sharing living space with ancient Romans. In the complex, you'll find roman baths, a roman forum, brothels, basilicas, a grand theater, and the oldest Roman amphitheater in the world.


When you're done exploring the ruins, head to a vineyard or restaurant on the nearby Mount Vesuvius.



the Grand Canal in venice, with the Doge's Palace on the left


26. Venice: the Romantic Floating City


I started with one of Italy's most fascinating towns -- Florence -- and I end with another showstopper -- Venice. Venice is truly unique. It's one of the world's most beautiful and captivating cities, a natural movie set. No other place looks quite like it. Venice is a city built on water that shouldn't exist in real life.


The most popular sites are in the San Marco area. Start with the spectacular Italo-Byzantine church of St. Mark's. It's one of Europe's most stunning churches with 90,000 feet of mosaics.


Take the Secret Itineraries tour of the Doge's Palace, once the home of Venice's titular leader and now the government center. The tour takes your through secret chambers, the prison cell of Casanova, and the Bridge of Sighs.






But Venice is so much more than San Marco. To escape the crowds head to the rustic Dorsoduro area and visit the world famous Peggy Guggenheim Museum.


Stroll through the Cannareggio district, where you can learn to row a gondola. In Cannareggio, you can pop into the Galleria dell'Academia, which houses the world's most famous painting, Leonardo da Vinci's Vitruvian Man.


If you're interested in Italy travel, here are few of my other popular guides:


Rome in 3 Days

Rome in 5 Days

Best Archaeological Sites in Rome

Hidden Gems in Rome

Must See Sites in Florence

Guide to the Uffizi Gallery

Must See Sites in Venice

Must See Sites in Siena

Must See Art in Tuscany

Best Museums in Rome

Best Museums in Florence

Best Museums in Italy

Must See Masterpieces at the Vatican


If you'd like to explore Italy's most beautiful towns, pin it for later.